Pyridine → N-[5-(3-fluorobenzenesulfonylamino)-1H-indazol-3-yl)acetamide

HRID 25393Notes

Reaction equation

HRID 25393 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]1[CH:7]=[C:8]([S:12]([NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[C:19]3[NH2:25])(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1.N1C=CC=CC=1>O>[F:5][C:6]1[CH:7]=[C:8]([S:12]([NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[C:19]3[NH:25][C:1](=[O:3])[CH3:2])(=[O:13])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22319642HCID 22319642, compound

Product 1

HCID 22567109N-[5-(3-fluorobenzenesulfonylamino)-1H-indazol-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

N-[5-(3-Fluorobenzenesulfonylamino)-1H-indazol-3-yl)acetamide can be obtained in the following way: 0.037 ml of acetyl chloride is added dropwise to a solution, cooled to 0° C., of 0.16 g of 3-fluoro-N-(3-amino-1H-indazol-5-yl)benzenesulfonamide and of 3.2 ml of pyridine. The reaction medium is then maintained with stirring at a temperature in the region of 25° C. overnight. After addition of 20 ml of water, the medium is extracted with three times 10 ml of ethyl acetate. The pooled organic phases are dried over magnesium sulfate, filtered and concentrated by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a silica column with a dichloromethane/methanol (97.5/2.5 by volume) mixture as eluent. The solid obtained is recrystallized from 6 ml of isopropanol. 0.1 g of N-[5-(3-fluorobenzenesulfonylamino)-1H-indazol-3-yl)acetamide is thus obtained, after drying under reduced pressure at 60° C., in the form of a white solid melting at 246° C. (analysis C15H13FN4O3S.0.2H2O % calculated C, 51.73, H, 3.76; F, 5.45; N, 16.08; O, 13.78; S, 9.20. % found C, 51.75; H, 2.82; F, 5.07; N, 16.04; S, 8.13).

Workup

  1. temperatureThe reaction medium is then maintained
  2. extractionthe medium is extracted with three times 10 ml of ethyl acetate
  3. dry with materialThe pooled organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by chromatography on a silica column with a dichloromethane/methanol (97.5/2.5 by volume) mixture as eluent
  8. customThe solid obtained
  9. customis recrystallized from 6 ml of isopropanol

Sources & evidence

ORD record
ord-2fc8d60f288c41f283dc6cca09a2560e
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

Loading…